The bulk of a puffer jacket makes it tough to get shoulder and crossbody bags to lay flat; instead, try a practical—but cute!—structured leather backpack.
Metallic Puffer Jacket, $190, us.topshop.com.
Mini Leather Drawstring Bag, $58, asos.com.
Meet the clean lines of a bomber with a streamlined bag in an unexpected shape.
Satin Bomber Jacket, $40, hm.com.
Circular Leather Bag, $125, cosstores.com.
Contrast the toughness of a leather moto jacket with a sweet little crossbody bag. Look for one with a removable strap, so you can carry it as a clutch to further the macho-elegant extreme.
Acne Studios Mock Leather Biker Jacket, $1,650, matchesfashion.com.
Karl Lagerfeld Kocktail Leather-Trimmed Faux Textured-Leather Shoulder Bag, $295, net-a-porter.com.
The rigid shape of the boxy bag balances the soft fur of the coat, while the two are united by the fact that each piece looks like it could have been plucked from the closet of a fancy lady (feel free to offset that vibe with tattered jeans or a pair of classic Chucks).
Leo Faux Fur, $275, stories.com.
Mini Sun Bag, $1,095, mansurgavriel.com.
Polished and confident, this duo is a truly timeless.
Babaton Macauley Jacket, $195, aritzia.com
Port of Call Clutch in Red Crush, $295, shop.lizziefortunato.com.
Utility, utility, utility. Even with a bow on it (like the Zara style, below), jean jackets are no nonsense. Honor that with a big, colorful shopper and conquer those weekend errands.
Denim Jacket With Bow, $50, zara.com.
Multi-Stripe Tote Bag, $150, jcrew.com.
Perhaps you've picked up on a theme here: Opposites attract. Here, a rough-and-tumble army jacket is offset by a little pink, hyper-embellished bag with a chain strap.
Camo Jacket, $50, ae.com.
Dinky Bag, $695, coach.com.
Fanny packs—sometimes dressed up with the term "belt bags"—are divisive. You love 'em or you hate them. Should you fall in the former category, display yours with pride with a long coat worn open.
Unstructured Wool Coat, $100, mango.com.
Alexander Wang Dumbo Rose Embossed Fanny Pack, $510, openingceremony.com.